It might sound like a silly question. The NCAA Tournament is on the short list of the most exciting sporting events, and it's an annual tradition we all know and love — except when our team loses in heartbreaking fashion. Or a team we loathe wins it all. Or we lose a bracket pool. Or all those things happen at once. March Madness can break your heart, right?

Take the 1993 tournament, best known for Chris Webber's ill-fated timeout in the national championship game against North Carolina in 1993. That's a heartbreaker neither Michigan fans — nor then-seventh-graders who filled out (and would have won their mother's bracket in a way-too-lucrative pool) — will ever forget.

Seriously, Mom still blames me for that timeout.

With that in mind, Sporting News staff members answer the question: When did March Madness break our hearts? Here are our best stories.

Why aren't they on TV? Notre Dame (1974)

"I could sound way too much like a sportswriter and say the biggest NCAA Tournament heartbreak for me was the time in 1997 when West Virginia's Jarrod West banked in a 30-foot 3-pointer — with help from Cincinnati forward Ruben Patterson's fingertip taking the spin off the ball — and cost me a week in Southern California and probably 15,000 Marriott points. But even then, I wound up in Greensboro covering the phenomenal UConn-Washington game that ended with Rip Hamilton's crazy fallaway.

The truth is, I move on as long as the tournament does.

I haven’t been a fan of a particular college basketball team since I was a teenager in the 1970s. I grew up in an Irish Catholic household and was therefore almost a Notre Dame fan by default. The Irish were pretty much the only team whose games were regularly on television, and they had compelling players such as Austin Carr and Adrian Dantley, so they were easy to love.

Their 1974 team was legitimately great. Even entering the NCAAs with two losses, the Irish probably weren't going to win the NCAA Championship in a field that included David Thompson’s N.C. State and Bill Walton’s UCLA, but it probably ought to have done better than a double-digit Sweet 16 loss to Michigan. How much could my heart be broken, though, if I couldn't even see it happen? All the games weren't available on TV then, and Irish-Wolverines game was not shown in Pittsburgh. It was just a disappointing score line. I still don't understand how Dantley could go 1 of 7 from the field, but it happened.

I can tell you this: I wasn't so devastated that I didn’t thoroughly delight in N.C. State's overtime Final Four victory over UCLA. What an incredible game that was. It always has been about the game for me." — Mike DeCourcy

Purple Pain: Northwestern (2017)

"Heartbreak is always part of the territory as a Northwestern sports fan, even when things are going surprisingly awesome. The good news is, because the Wildcats never made the NCAA Tournament before '17, our March misery is milder than most. Still, after knocking off Vandy to win our first game in our first Big Dance, it was easy to be greedy for more as we pushing top-seeded Gonzaga to the brink in Salt Lake City. Our big second-half comeback was sadly derailed, however, by a ridiculously blown goal-tending call from the Bulldogs' Zach Collins. It felt worse when the NCAA admitted it was a glaring officiating mistake in a close game, a 79-73 loss.

Even worse was having a March Madness hangover and not living up to the expectations of a top-25 team the following season, becoming a sub-.500 team once again. Who needs a drink?" — Vinnie Iyer

Beltway Blues: Georgetown (1982, 1985) and Maryland (2001)

"A three-way tie if possible. Fred Brown against North Carolina. Villanova basically not missing a shot against Georgetown. Maryland's 22-point lead disappeared little by little against Duke in the 2001 Final Four).

If I had to put one at No. 1, the Duke game would edge them out. After everything we had been through for 15 years after Len Bias died, getting to the Final Four, having a chance to win a national championship and going through Duke to do it was inconceivable. I'm not totally sure that the happiness of seeing them win it all the next year is as powerful as the agony of seeing them lose that lead in the second half in typical Duke fashion (including seeing every single possible call go their way, and hearing Jim Nantz all but cheer them on the entire way). It was like having 22 of your teeth pulled without Novocaine.

Tough call, though. The tiebreaker was my being a Maryland grad who was there when Bias was there. But I loved Georgetown equally as much for different reasons. Seeing them lose to Carolina the way they did in 1982 was excruciating. But losing in '85 — as the defending champ and overwhelming favorite to repeat, as America's villain and most-hated team for all the crappy reasons they were, after four years of John Thompson being called 'Idi Amin' and Patrick Ewing having 'You Can't Read' signs waved at him for four years — to a Villanova team that was portrayed as so lovable and huggable only because of who they were playing. ... I couldn't even root for them a couple of years ago against North Carolina. I wanted them both to lose. I will never forgive them for what they did. People treated it as if it was the Miracle on Ice, and Georgetown was the Russians. OK, enough venting for me." – David Steele

'4.8': Missouri (1995)

"I will probably always hate the number 4.8. I was on a spring break ski trip in Colorado when 4.8 became forever ingrained in my brain. I grew up in suburban St. Louis, watching the great Mizzou teams with Anthony Peeler and Doug Smith when they were on TV, but mostly listening on the radio. The NCAA Tournament had only offered heartbreak for the Tigers, but on one day in 1995, everything felt different. This wasn't one of Norm Stewart's best teams; this group couldn't match the talent on that top-seeded UCLA team — the O'Bannon brothers were so good it wasn't fair, the Bruins had an unending supply of big men and a point guard who shall remain nameless — but Norm's crew played a nearly flawless game.

They dropped whatever hero-shot tendencies they harbored during an up-and-down season in favor of a well-orchestrated passing attack that created smart, open looks at the hoop, especially beyond the 3-point arc, and they knocked down those opportunities. They valued the basketball. They controlled the tempo. They blocked out and kept UCLA from getting easy put-back buckets. They did every single thing they needed to do to have a chance against a No. 1 seed most people expected to win the national championship. And they took a 74-73 lead on a brilliantly executed play, when Kendrick Moore dropped a pass to Julian Winfield in the lane and Winfield converted. UCLA called a timeout.

With 4.8 seconds left.

Ugh. I remember thinking to myself, "That's not enough time to get all the way down the court, right? They're going to have to attempt something deep, right?" Turns out, 4.8 seconds was exactly the right amount of time for Tyus Edney to race down the court, shake a defender at midcourt with a behind-the-back dribble and put up a game-winning layup off the glass, over the outstretched arms of big man whose primary goal was pretty clearly not to foul.

Dammit, 4.8." — Ryan Fagan

2-15 disaster: Missouri (2012)

"Mizzou fans are used to losing. Not just losing, but losing in dramatic and creative ways. Yeah, everyone's school suffers heartbreaking losses, but Mizzou's have nicknames: 'Fifth Down', 'Flea Kicker', '4.8'. Well, 2012 was supposed to be different. Fresh off a Big 12 Conference Tournament title (in its last year in the Big 12), Mizzou was a strong No. 2 seed that many were picking to go to the Final Four for the first time in school history. A first-round matchup against Norfolk State was barely even a blip on the radar. Mizzou fans were already looking ahead to an Elite 8 matchup with Michigan State.

But we should have known better. Perhaps most frustrating was that Mizzou didn't lose in a memorable way — it just got beat by a solid Norfolk State team that seemingly couldn't miss. Future NBA player Kyle O'Quinn dominated inside while Big 12 Tournament MVP Kim English went 1 for 7. Mizzou had a chance to win it, down two with 2.9 seconds left, but Phil Pressey's 25-foot heave clanked off the rim as the buzzer sounded and Norfolk State celebrated one of the biggest upsets in Tournament history.

And just like that, it was over. That big March run we were all gearing up for was just another footnote in Mizzou's history of agony. In classic Mizzou fashion, No. 2 seed Duke lost later that evening to Lehigh, so Missouri wasn't even the most memorable upset of the day. Sadly, when you don't have many positive things to hang your hat on, you start taking pride in the negatives, 'Hey, at least we're the biggest losers.' We couldn't even claim that. I can't think of a better way to sum up being a Mizzou fan." –- Matt Lutovsky

Tar-Heeled: Ohio (2012)

"When you go to a Mid-American Conference school, a Sweet 16 feels like a Final Four and an Ohio win against North Carolina in 2012 would have felt like a national championship. I lived in Charlotte at the time and put up with the smug dismissiveness of the Tar Heel fans all week despite a key injury to Kendall Marshall. That was fine. This wasn't a happy-to-be-there-as-a-13-seed situation. This was a ‘Let's go to the Elite Eight and party on Court Street'-type deal. After all, the Bobcats beat the Tar Heels in Chapel Hill, N.C., my senior year on Feb. 20, 2002.

Seriously, that happened. Look it up.

This one should have happened, too, despite a 20/20 game by Tyler Zeller. Ohio should have won, but MAC schools know you could leave a ‘should have' out there. Harrison Barnes hit a go-ahead 3-pointer, and the Bobcats missed a go-ahead free throw in the final minute. This was a game that couldn't go to overtime, and the Heels won 73-65 when it did. No, I wasn't happy to be there. I'm still mad Ohio lost the damn game." –- Bill Bender

What's tournament pain like? Rutgers and Butler (2010)

"I went to Rutgers. Need I say more? ‘Rutgers' and ‘winning' go together as well as a toaster and a bathtub. Really: Scarlet Knight men's hoops has only made the NCAA Tournament six times in its ‘illustrious' history, last making it to one in 1991, just a few months after I was brought into this cursed sports world. They have a NCAA Tournament record of 5-7, so basically, a better record than your average season of RU football.

My rip-my-heart-out moment was watching my adopted tourney squad (sue me), the 2009-2010 Butler Bulldogs on their Cinderella run, and Gordon Hayward coming within inches of giving Butler the win over that damned Kyle Singler and the Blue Devils. Of course, my hatred of Duke is born out of envy, so watching tournament MVP Singler get blown up by Butler's Matt Howard on a pick on the last possession put a smile on my face after I emerged from my jealous rage. I won't admit that it still does (it does)." — Joe Rivera

Yes, 'The Shot' is on here: Kentucky (1992)

"No. I'm not a Kentucky fan, but growing up my favorite college basketball team was Michigan and anyone who was playing against Duke. Why? You already know why. I hate(d) Christian Laettner ... and Bobby Hurley and Brian Davis. Grant Hill was cool, but he rolled with a bunch of dudes I couldn't stand. So, I had to dislike him by association. In my opinion, they, with their too short shorts, perfectly coiffed hair and Seinfeld-white sneakers, represented the establishment. I always say rooting for Duke is like rooting for the IRS in an audit. Michigan's Fab Five was the first college basketball team I really latched on to with their bald heads, baggy shorts, black shoes and socks and playground bravado. They represented hip-hop, a culture I was all but born into and was starting to identify with.

Every time I see Laettner looking like a tall, long-lost member of New Kids on the Block, catch that perfectly thrown pass from Hill, put down one dribble and knock down that perfect turn-around jumper at the buzzer in the 1992 regional final, it still grinds my gears." — Nick Birdsong

Hog hell: Duke (1994)

"As a Duke fan, Scotty Thurman's go-ahead 3 for Arkansas with less than a minute left in the 1994 title game was a dagger through the heart. I know, I know, 'Poor Duke fan.' But I still don’t know how that rainbow shot cleared the outstretched fingertips of Antonio Lang, much less how it went in. Still, I was sure Duke would answer with its own miracle shot — after all, that was their thing in the '90s — but, sadly, there was no Christian Laettner to save the Blue Devils this time. I know, I know, 'Poor Duke fan.'" — Brad Pinkerton

Pittsnogled! Wake Forest (2005)

"Few remember West Virginia's 111-105 double-overtime victory against Wake Forest in the second round of the 2005 NCAA Tournament. For me, it's one of those remember-where-you-were games and, in this case, a remember-what-couch-you-punched game. I do not and have never considered myself a Wake Forest fan; it's the timing of this particular matchup that was important. My family two years prior had moved from Parkersburg W.V., to Winston-Salem N.C., home of the Demon Deacons. Wake Forest sophomore point guard Chris Paul had recently graduated from West Forsyth High School, which I would attend as a freshman later that year. I couldn't wait to watch the Deacs bounce the Mountaineers out of the Big Dance so I could brag to my childhood friends back in West Virginia.

Then Kevin Pittsnogle hit that damn 3-pointer.

While Pittsnogle's 3 was the dagger that gave WVU a seven-point lead late in double overtime of a back-and-fourth game, Mike Gansey stole the show with 19 of his 29 points in the two overtime periods. To this day, I tell my friends Wake Forest easily would have won had Paul not fouled out with a little more than three minutes to play in the second overtime. In hindsight, maybe I was just bitter because the team I was rooting for was buried by a man named Kevin Pittsnogle." — Tadd Haislop

(Not so) Sweet 16: Pitt (2011)

"It was 2011, and Pitt was a No. 1 seed. As soon as we saw the schedule my friends booked a trip to New Orleans for WHEN Pitt reached the Sweet 16. We watched their Round of 32 game against Butler at a bar in NYC, heavily invested with a $400 flight locked in.

Shelvin Mack went nuts and lit us up with seven 3s while Pitt's star scorer Ashton Gibbs attempted just seven shots the entire game, a vintage showcase of Jamie Dixon's in-game strategic shortcomings. Pitt still ended up with the ball and a chance to win, down one point with two seconds left. Gilbert Brown drew a controversial foul call near midcourt, and tied it with the first free throw. He missed the second and Butler's Matt Howard pulled down the rebound, only to be fouled by Pitt forward Nasir Robinson's reaching arms — 93 feet from the basket. Howard sank his first free throw and the game was over.

We still ended up making that trip to New Orleans, drinking our pain away throughout, and got to see Jimmer Fredette pour in 32 at the Superdome. Butler ended up making a repeat appearance in the national championship before losing to Kemba Walker and UConn, who coincidentally knocked Pitt out of the Big East tournament that year. Pitt hasn't sniffed a high seed in the tourney since that season." — Alex Novick